54911-85-2Relevant academic research and scientific papers
Double cationic propargylation: From linear to polycyclic ethers
Diaz, David,Martin, Tomas,Martin, Victor S.
, p. 3289 - 3291 (2001)
Equation presented The trapping of cations generated from Co2(CO)6-bispropargylic alcohols provided diethers in good yield. The procedure is also valid when two vicinal acetylenes are present. The methodology can be applied to the sy
Synthesis of norpandamarilactonines, pandamarilactonines, and pandanamine
Gogoi, Sanjib,Argade, Narshinha P.
, p. 1455 - 1459 (2008)
A facile route to naturally occurring (±)-norpandamarilactonines A and B, (±)-pandamarilactonines A-D, and pandanamine has been described from 3-methylfuran-2(5H)-one, with a reductive intramolecular aza-Michael-type addition as the key step. Georg Thieme Verlag Stuttgart.
A scalable synthesis of (+)-coronafacic acid
Kato, Nobuki,Miyagawa, Saki,Nomoto, Haruna,Nakayama, Misuzu,Iwashita, Makoto,Ueda, Minoru
, p. 423 - 430 (2020)
A facile, efficient, and scalable synthesis of optically pure coronafacic acid by resolution of racemic coronafacic acid obtained using an improved version of Watson's method has been developed. By optimizing the boron-mediated aldol reaction of Watson, we were able to prepare 2.1 g of racemic coronafacic acid. This was coupled with (S)-4-isopropyl-2-oxazolidinone to give a mixture of diastereomeric coronafacyl oxazolidinones, which were readily separable by silica-gel column chromatography to give 630 mg of optically pure (+)-coronafacic acid.
Oxidation of monotetrahydropyranylated short-chain symmetrical diols
Petroski, Richard J.
, p. 3243 - 3250 (2003)
The free hydroxyl functions of monotetrahydropyranylated three-to five-carbon symmetrical primary diols are oxidized to aldehydes, without cleavage of the protective group, by using pyridinium dichromate in CH 2Cl2 and anhydrous MgSO4 as a water scavenger. The oxidation procedure is improved for these specific compounds since over oxidation to carboxylic acids and formation of dimeric esters are suppressed.
4-Methyltetrahydropyran (4-MeTHP): Application as an Organic Reaction Solvent
Kobayashi, Shoji,Tamura, Tomoki,Yoshimoto, Saki,Kawakami, Takashi,Masuyama, Araki
, p. 3921 - 3937 (2019/11/11)
4-Methyltetrahydropyran (4-MeTHP) is a hydrophobic cyclic ether with potential for industrial applications. We herein report, for the first time, a comprehensive study on the performance of 4-MeTHP as an organic reaction solvent. Its broad application to organic reactions includes radical, Grignard, Wittig, organometallic, halogen-metal exchange, reduction, oxidation, epoxidation, amidation, esterification, metathesis, and other miscellaneous organic reactions. This breadth suggests 4-MeTHP can serve as a substitute for conventional ethers and harmful halogenated solvents. However, 4-MeTHP was found incompatible with strong Lewis acids, and the C?O bond was readily cleaved by treatment with BBr3. Moreover, the radical-based degradation pathways of 4-MeTHP, THP and 2-MeTHF were elucidated on the basis of GC-MS analyses. The data reported herein is anticipated to be useful for a broad range of synthetic chemists, especially industrial process chemists, when selecting the reaction solvent with green chemistry perspectives.
Synthesis method of aggregation pheromone (E)-cis-6, 7-epoxy-2-nonenal of Aromia bungii
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Paragraph 0030; 0031; 0032; 0033; 0034; 0035, (2019/05/08)
The invention relates to a synthesis method of aggregation pheromone (E)-cis-6, 7-epoxy-2-nonenal of Aromia bungii, which belongs to the field of pharmaceutical synthesis. The synthesis method comprises the following steps: taking 1, 4-butanediol as a raw material, singly protecting diol with DHP (dihexylphthalate) and then oxidizing TEMPO (tetramethylpiperidine oxide) into 4-((tetrahydro-2H-pyran-2-base) oxy) butyraldehyde; performing a Wittig reaction, so as to obtain (Z)-2-(hepta-4- alkene-1-base-oxy) tetrahydro-2H-pyran; removing the protection of the DHP and oxidizing TEMPO, so as to obtain (Z)-4-heptenal; performing a Wittig reaction, so as to obtain (2E, 6Z)-nona-2, 6-heptadienal; finally, performing epoxidation, so as to obtain the aggregation pheromone (E)-cis-6, 7-epoxy-2-nonenalof the Aromia bungii. The total yield is 6.5%. In the synthesis method, the 1, 4-butanediol with low cost is taken as the starting raw material; the synthesis method has the advantages of being simple in operation and mild in conditions, therefore, the synthesis method is suitable for large-scale preparation.
Au-catalyzed intramolecular hydroalkoxylation of gem-difluorinated alkynols
Hamel, Jean-Denys,Paquin, Jean-Fran?ois
, p. 11 - 23 (2018/10/20)
The intramolecular hydroalkoxylation of gem-difluorinated alkynols was found possible under Au catalysis, allowing for the preparation of a series of fluorinated heterocycles. The nature of the solvent was found to be especially critical in the cyclizatio
ERK INHIBITORS
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Page/Page column 84-85, (2016/07/05)
The present invention provides a compound of Formula (I) or the pharmaceutically acceptable salts, esters, and prodrugs thereof, which are ERK2 inhibitors. The invention also provides a method of inhibiting ERK2 in a patient in need of such treatment comprising administering to said patient an effective amount of at least one compound of Formula (I). The invention also provides a method for treating cancer in a patient in need of such treatment, said method comprising administering to said patient an effective amount of at least one compound of Formula (I).
Silver-mediated exo-selective tandem desilylative bromination/ oxycyclization of silyl-protected alkynes: Synthesis of 2-bromomethylene- tetrahydrofuran
Lee, Hyun-Ji,Lim, Chaemin,Hwang, Soonho,Jeong, Byeong-Seon,Kim, Sanghee
experimental part, p. 1943 - 1947 (2011/11/30)
Three in one: The exocyclic β-bromo enol ether is a synthetically useful functional moiety in the preparation of functionalized oxygen heterocycles. A new tandem method for the synthesis of this valuable moiety has been achieved by employing silyl-protect
Copper-catalyzed olefin aminoacetoxylation
Mancheno, Danny E.,Thornton, Aaron R.,Stoll, Armin H.,Kong, Aidi,Blakey, Simon B.
supporting information; experimental part, p. 4110 - 4113 (2010/11/04)
A new catalyst system for intramolecular olefin aminoacetoxylation is described. In contrast to previously reported palladium- and copper-catalyzed systems, the conditions outlined in this communication favor piperdine formation with terminal olefin subst
